pentamidine Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
2090 100-33-4

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • pentamidine isetionate
  • pentamidine diisethionate
  • pentamidine
  • pentamidine isethionate
  • pentamidin
  • pentamidine mesylate
  • pentamidine mesilate
Antiprotozoal agent effective in trypanosomiasis, leishmaniasis, and some fungal infections; used in treatment of PNEUMOCYSTIS pneumonia in HIV-infected patients. It may cause diabetes mellitus, central nervous system damage, and other toxic effects.
  • Molecular weight: 340.43
  • Formula: C19H24N4O2
  • CLOGP: 2.31
  • LIPINSKI: 0
  • HAC: 6
  • HDO: 4
  • TPSA: 118.20
  • ALOGS: -4.16
  • ROTB: 10

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
0.28 g P

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 100 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 12 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 11.75 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 0 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 53 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 74 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.09 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 25 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Oct. 16, 1984 FDA FRESENIUS KABI USA

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Pneumocystis jirovecii pneumonia 98.78 54.33 15 50 2258 2355762

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Pneumocystis jirovecii pneumonia 56.28 51.23 11 97 2445 1744228
Bronchospasm 51.81 51.23 10 98 2072 1744601

Pharmacologic Action:

SourceCodeDescription
ATC P01CX01 ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
ANTIPROTOZOALS
AGENTS AGAINST LEISHMANIASIS AND TRYPANOSOMIASIS
Other agents against leishmaniasis and trypanosomiasis
FDA EPC N0000175485 Antiprotozoal
MeSH PA D000890 Anti-Infective Agents
MeSH PA D000935 Antifungal Agents
MeSH PA D000977 Antiparasitic Agents
MeSH PA D000981 Antiprotozoal Agents
CHEBI has role CHEBI:36335 trypanocidal drug
CHEBI has role CHEBI:67079 anti-inflammatory agent
MeSH PA D014344 Trypanocidal Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
African trypanosomiasis indication 27031003 DOID:10112
Pneumocystosis jiroveci pneumonia indication 415125002 DOID:11339
Pneumocystis Carinii Pneumonia Prevention indication
Visceral leishmaniasis off-label use 186803007 DOID:9146
Cutaneous leishmaniasis off-label use 240637006 DOID:9111
Hypocalcemia contraindication 5291005
Hyperkalemia contraindication 14140009
Torsades de pointes contraindication 31722008
Dehydration contraindication 34095006
Hypertensive disorder contraindication 38341003 DOID:10763
Conduction disorder of the heart contraindication 44808001
Low blood pressure contraindication 45007003
Diabetes mellitus contraindication 73211009 DOID:9351
Hyperglycemia contraindication 80394007 DOID:4195
Leukopenia contraindication 84828003 DOID:615
Kidney disease contraindication 90708001 DOID:557
Liver function tests abnormal contraindication 166603001
Hypomagnesemia contraindication 190855004
Asthma contraindication 195967001 DOID:2841
Acute pancreatitis contraindication 197456007 DOID:2913
Disease of liver contraindication 235856003 DOID:409
Toxic nephropathy contraindication 236514003
Hypoglycemic disorder contraindication 237630007
Anemia contraindication 271737000 DOID:2355
Thrombocytopenic disorder contraindication 302215000 DOID:1588

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 11.38 Basic
pKa2 10.78 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Alpha-2A adrenergic receptor GPCR Ki 6.29 DRUG MATRIX
Potassium voltage-gated channel subfamily H member 2 Ion channel Ki 4.89 DRUG MATRIX
Sodium-dependent noradrenaline transporter Transporter Ki 5.66 DRUG MATRIX
5-hydroxytryptamine receptor 2A GPCR Ki 6.33 DRUG MATRIX
5-hydroxytryptamine receptor 2C GPCR Ki 5.77 DRUG MATRIX
D(3) dopamine receptor GPCR Ki 5.87 DRUG MATRIX
Muscarinic acetylcholine receptor M2 GPCR Ki 6.29 DRUG MATRIX
Muscarinic acetylcholine receptor M4 GPCR Ki 6.66 DRUG MATRIX
Muscarinic acetylcholine receptor M5 GPCR Ki 5.68 DRUG MATRIX
Sodium-dependent dopamine transporter Transporter Ki 5.60 DRUG MATRIX
Alpha-1D adrenergic receptor GPCR Ki 6.31 DRUG MATRIX
Amine oxidase [flavin-containing] A Enzyme IC50 6.10 DRUG MATRIX
Solute carrier family 22 member 3 Transporter IC50 5.02 CHEMBL
Protein-tyrosine phosphatase 4A3 Enzyme IC50 4.27 CHEMBL
Solute carrier family 22 member 1 Transporter IC50 4.66 CHEMBL
Trypsin-1 Enzyme Ki 5.64 CHEMBL
Glutamate NMDA receptor; GRIN1/GRIN2A Ion channel IC50 6.14 CHEMBL
Solute carrier family 22 member 2 Transporter IC50 5.92 CHEMBL
Amiloride-sensitive amine oxidase [copper-containing] Enzyme Ki 6.54 CHEMBL
Suppressor of tumorigenicity 14 protein Enzyme Ki 5.94 CHEMBL
Protein S100-B Cytosolic other Kd 6 CHEMBL
Multidrug and toxin extrusion protein 2 Transporter IC50 5.57 CHEMBL
Multidrug and toxin extrusion protein 1 Transporter IC50 6.39 CHEMBL
Spermidine/spermine N(1)-acetyltransferase 1 Enzyme Ki 5.70 CHEMBL
Alpha-1B adrenergic receptor GPCR Ki 6.27 DRUG MATRIX
Acrosin Unclassified Ki 5.64 CHEMBL
Glutamate NMDA receptor Ion channel IC50 5.88 CHEMBL
Alpha-1A adrenergic receptor GPCR IC50 5.92 CHEMBL

External reference:

IDSource
4019043 VUID
N0000178948 NUI
C0030864 UMLSCUI
D00834 KEGG_DRUG
673LC5J4LQ UNII
4167 INN_ID
31692006 SNOMEDCT_US
4019881 VANDF
7933 MMSL
7994 RXNORM
372699006 SNOMEDCT_US
d00030 MMSL
6823-79-6 SECONDARY_CAS_RN
CHEMBL55 ChEMBL_ID
CHEMBL935 ChEMBL_ID
CHEMBL361506 ChEMBL_ID
DB00738 DRUGBANK_ID
CHEBI:45081 CHEBI
D010419 MESH_DESCRIPTOR_UI
4735 PUBCHEM_CID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Pentamidine Isethionate HUMAN PRESCRIPTION DRUG LABEL 1 13925-515 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 300 mg INTRAMUSCULAR ANDA 13 sections
Pentamidine Isethionate HUMAN PRESCRIPTION DRUG LABEL 1 13925-522 INHALANT 300 mg RESPIRATORY (INHALATION) ANDA 12 sections
Pentam 300 HUMAN PRESCRIPTION DRUG LABEL 1 63323-113 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 300 mg INTRAMUSCULAR NDA 13 sections
NebuPent HUMAN PRESCRIPTION DRUG LABEL 1 63323-877 INHALANT 300 mg RESPIRATORY (INHALATION) NDA 12 sections